Hydroxy aromatic ketones such as 4-hydroxyacetophenone (4-HAP) are possible intermediates for a variety of products having a multiplicity of end uses. Thus, pending U.S. application Ser. No. 06/618,659, filed June 8, 1984, discloses a process for using hydroxy aromatic ketones, such as 4-HAP to make N-acyl hydroxy aromatic amines such as N-acetyl-para-aminophenol (APAP), better known as acetaminophen, which has wide use as an analgesic. Pending U.S. application Ser. No. 06/627,382, filed July 3, 1984, discloses the use of hydroxy aromatic ketones such as 4-HAP as an intermediate for the production of N-acyl-acyloxy aromatic amines such as 4-acetoxyacetanilide (4-AAA) which can be used for the preparation of poly(ester-amide)s capable of forming an anisotropic melt phase and suitable for being formed into shaped articles such as moldings, fibers and films. In addition, 4-AAA may also be hydrolyzed to form APAP. Pending U.S. application Ser. No 06/633,832, filed July 24, 1984, discloses a process wherein hydroxy aromatic ketones such as 4-HAP are used to produce acyloxy aromatic carboxylic acids such as 4-acetoxybenzoic acid (4-ABA) which are also capable of being used directly to make polymers which can be formed into an anisotropic melt suitable for the formation of shaped articles. Moreover, 4-ABA can be hydrolyzed to 4-hydroxybenzoic acid (4-HBA) which can be used as an intermediate for the production of preservatives, dyes, and fungicides. Pending U.S. applications Ser. No. 06/661,552, filed Oct. 17, 1984, and Ser. No. 06/689,533, filed Jan. 7, 1985, disclose processes wherein hydroxy aromatic ketones such as 4-HAP are used as intermediates for the production of aromatic diols such as hydroquinone (HQ) which have utility as photographic developers, polymerization inhibitors, dye intermediates, and anti-oxidants.
Dann and Mylius in a dissertation included as part of a series of Reports from the Institute for Applied Chemistry of the University of Erlangen, received for publication on Jan. 7, 1954 and published in Annalen der Chemie 587 Band, pages 1 to 15, disclose the reaction of phenol and glacial acetic acid in the presence of hydrogen fluoride to produce 4-hydroxyacetophenone (4-HAP) in a yield of 61.6%. This reaction may be conventionally characterized as a Friedel-Crafts acetylation of phenol with acetic acid as the acetylating agent.
Simons et al, Journal of the American Chemical Society, 61, 1795 and 1796 (1939) teach the acylation of aromatic compounds using hydrogen fluoride as a condensing agent and in Table 1 on page 1796 show the acetylation of phenol with acetic acid to produce p-hydroxyacetophenone (4-HAP) in 40% yield.
European Patent Publication No. 69,597, published Jan. 12, 1983, discloses the preparation of p-phenoxybenzoyl compounds by reacting diphenyl ether and an appropriate acyl compound such as acetic anhydride in the presence of hydrogen fluoride.
Meussdoerffer et al, German Offenlegungsschrift No. 26 16 986 published Oct. 27, 1977 and assigned to Bayer AG, disclose the hydrogen fluoride-catalyzed acylation of phenolic compounds such as phenol itself with an acyl halide such as acetyl chloride to form hydroxy aromatic ketones.